The Cheapest Places to Fly This Winter

Named one of the cheapest places to fly in 2025 by Dollar Flight Club, Lisbon is a comparatively affordable European destination for US travelers year-round, particularly during the low months between November and March. TAP Portugal, its flag carrier, has some of the lowest fares across the Atlantic and, once there, food and accommodation are much lower than what you’ll find next door in Spain. The only catch? Hotels and homestays tend to fill up fast with Northern Europeans escaping winter at home, so it’s wise to book your lodgings as early as you can.

On average, round-trip airfare to Lisbon from major US airports is about $650. Searching from the East and West Coasts, Boston and San Francisco respectively, we found January flights for just $450, with nonstops on TAP going for $610 round-trip.

For a fuss-free winter getaway at the last minute, San Juan is a hard one to beat. Not only is this year-round paradise relatively easy to reach from much of the U.S., but, as a U.S. territory, your visit won’t require a passport or even a change of currency. Most importantly, for budget travelers, flights to Puerto Rico are inexpensive.

Flights can be had for under $280 round-trip, nonstop, on legacy carriers from major East Coast cities, with certain dates in January seeing fares below $200. If departing from the West Coast, you can expect to pay around $270 for the absolute cheapest flight (yes, that will involve a connection), but most round-trip fares will run you closer to $330. According to Skyscanner data, prices for a March visit to San Juan are trending downward, with fares this year dropping 20% from 2024.

A long weekend of reliable sunshine, swimming pools, and excellent tacos are sometimes all you need to break through a seasonal funk. L.A. has plenty of all three and is the gateway to other SoCal attractions like Disneyland and nearby Palm Springs and Joshua Tree. While California doesn’t have a reputation as a budget destination, there has never been a better time to book a trip to the Sunshine State on a budget. Data from Skyscanner shows that year-over-year domestic fares to LAX dropped 14% in February and 29% in March of 2025.

Flights departing from major East Coast airports to LAX range from $150 to $250, with fares generally becoming cheaper as you move to hubs further west. Flights from Denver, Houston, Dallas, Portland, and Salt Lake City are available for less than $100 round-trip.

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Dollar Flight Club ranks Reykjavik as one of the cheapest places to fly in 2025 and with the stunning Northern Lights, beautiful ski slopes, and icy landscape, fans of cold-weather travel shouldn’t miss an affordable visit during the winter off-season. The Icelandair Stopover program offers another cheap way to see the city, letting travelers build in an overnight visit to Reykjavik to their existing flight plans.

Nonstop, round-trip fares on Icelandair departing from the East Coast start as low as $299, with lower fares showing up in early December and early February. Prices are higher from the West Coast and central US hubs, but round-trip flights can still be found for under $600 for travelers willing to depart mid-week.

When the decision fatigue sets in and you feel incapable of choosing a sunny winter getaway, the right choice is sometimes the most obvious. Visitors to Florida will find plenty of coastline to go around, reasonably-priced accommodations for every budget, and more than enough flights to transport you cheaply to one of the three big local airports in Miami, Ft. Lauderdale, or West Palm Beach. Orlando — one of the cheapest domestic destinations for US travelers to fly year-round — ranks alongside Miami and Tampa for cheap winter getaways this holiday season, according to holiday travel data from Dollar Flight Club.

From Chicago (ORD), we were able to find February flights to Orlando (MCO) on Spirit for just $71 round-trip for travelers willing to arrive and depart midweek. Flights for the same dates on American were a close second at $92 round-trip. Flights from other East Coast airports can be found easily for under $150, with some dipping as low at $60 round-trip as you move further south. Flights from the West Coast remain mostly below $200.

Tracy Stewart contributed to this story.

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